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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:12:24 UTC

Update Date

2021-09-26 22:59:13 UTC

HMDB ID

HMDB0248759

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Azacyclonol

Description

Azacyclonol belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. It is made by the organometallic addition of 4-bromopyridine to benzophenone, followed by catalytic hydrogenation of the pyridine heteroaromatic ring system to the corresponding piperidine. It has also been called a tranquilizer and antipsychotic, though these definitions are not accurate as it does not actually possess such properties. Azacyclonol is a very strong basic compound (based on its pKa). Terfenadine produces azacyclonol as a major active metabolite. The drug was introduced in Europe in the mid-1950s for the treatment of schizophrenia likely because it was found to attenuate the subjective psychedelic effects of LSD and mescaline in humans. However, due to poor and mixed clinical effectiveness it never gained widespread acceptance and was eventually discontinued. Despite being a positional isomer of pipradrol, it is not a psychostimulant, and instead has mild depressant effects. This compound has been identified in human blood as reported by (PMID: 31557052 ). Azacyclonol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Azacyclonol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0248759
     RDKit          3D
Azacyclonol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.6853   -0.1292   -2.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4158   -0.0880   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    1.2406   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    1.8540    1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630    3.1017    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    3.8190    0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    3.2741   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    2.0383   -1.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564   -1.2183   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -2.2900   -0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -3.4122   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -3.4553    0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070   -2.4195    1.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.3122    1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -0.4027   -0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    0.6131   -1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231    0.0119   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712    0.3013    0.1334 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009    0.1317    1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -0.7759    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.3619   -2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.3376    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056    3.5557    2.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1184    4.8267    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225    3.8613   -1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.6459   -1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -2.3190   -1.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3374   -4.2375   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029   -4.3450    1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593   -2.4853    2.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -0.5033    1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.3222   -1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516    1.6073   -0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449    0.5769   -2.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880    0.4067   -1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.0988   -1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -0.0776    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -0.3806    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400    1.0930    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267   -1.8005    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -0.8617    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 20 15  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END

  Mrv1572004221604412D          

 20 22  0  0  0  0            999 V2000
    0.1105    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    4.3164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    4.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248759

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C1CCNCC1)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO/c20-18(15-7-3-1-4-8-15,16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,17,19-20H,11-14H2

> <INCHI_KEY>
ZMISODWVFHHWNR-UHFFFAOYSA-N

> <FORMULA>
C18H21NO

> <MOLECULAR_WEIGHT>
267.372

> <EXACT_MASS>
267.1623143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.59455178521684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
diphenyl(piperidin-4-yl)methanol

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.8795442826666666

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.219389687581298

> <JCHEM_PKA_STRONGEST_BASIC>
10.044802739817703

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
82.22170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azacyclonol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0248759
     RDKit          3D
Azacyclonol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.6853   -0.1292   -2.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4158   -0.0880   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    1.2406   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    1.8540    1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630    3.1017    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    3.8190    0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    3.2741   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    2.0383   -1.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564   -1.2183   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -2.2900   -0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -3.4122   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -3.4553    0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070   -2.4195    1.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.3122    1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -0.4027   -0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    0.6131   -1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231    0.0119   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712    0.3013    0.1334 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009    0.1317    1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -0.7759    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.3619   -2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.3376    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056    3.5557    2.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1184    4.8267    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225    3.8613   -1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.6459   -1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -2.3190   -1.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3374   -4.2375   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029   -4.3450    1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593   -2.4853    2.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -0.5033    1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.3222   -1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516    1.6073   -0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449    0.5769   -2.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880    0.4067   -1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.0988   -1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -0.0776    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -0.3806    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400    1.0930    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267   -1.8005    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -0.8617    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 20 15  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       0.206  12.677   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.127  11.907   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540  11.907   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   4.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   4.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.127  10.367   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540  10.367   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.540   5.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.127   5.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.104   9.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.104   6.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.644   9.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.644   6.724   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.206   9.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.206   6.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   8.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.206   8.057   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -4.414   8.057   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       1.746   8.057   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   15                                                       
CONECT    8    4   15                                                       
CONECT    9    5   16                                                       
CONECT   10    6   16                                                       
CONECT   11   13   17                                                       
CONECT   12   14   17                                                       
CONECT   13   11   19                                                       
CONECT   14   12   19                                                       
CONECT   15    7    8   18                                                  
CONECT   16    9   10   18                                                  
CONECT   17   11   12   18                                                  
CONECT   18   15   16   17   20                                             
CONECT   19   13   14                                                       
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0248759
HETATM    1  O1  UNL     1      -0.685  -0.129  -2.031  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.416  -0.088  -0.628  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.845   1.241  -0.202  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.535   1.854   1.000  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.963   3.102   1.366  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.754   3.819   0.505  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.095   3.274  -0.691  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.656   2.038  -1.023  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.156  -1.218  -0.069  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.440  -2.290  -0.887  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.133  -3.412  -0.473  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.562  -3.455   0.835  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.307  -2.420   1.689  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.608  -1.312   1.231  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.041  -0.403  -0.562  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.913   0.613  -1.319  1.00  0.00           C  
HETATM   17  C16 UNL     1       3.323   0.012  -1.190  1.00  0.00           C  
HETATM   18  N1  UNL     1       3.771   0.301   0.133  1.00  0.00           N  
HETATM   19  C17 UNL     1       2.801   0.132   1.142  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.630  -0.776   0.739  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.650  -0.362  -2.125  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.076   1.338   1.696  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.706   3.556   2.311  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.118   4.827   0.764  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.723   3.861  -1.356  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.957   1.646  -1.996  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.126  -2.319  -1.942  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.337  -4.238  -1.147  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.103  -4.345   1.138  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.659  -2.485   2.716  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.408  -0.503   1.891  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.161  -1.322  -1.228  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.852   1.607  -0.881  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.645   0.577  -2.407  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.988   0.407  -1.967  1.00  0.00           H  
HETATM   36  H16 UNL     1       3.254  -1.099  -1.288  1.00  0.00           H  
HETATM   37  H17 UNL     1       4.694  -0.078   0.386  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.277  -0.381   2.029  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.440   1.093   1.522  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.127  -1.801   0.719  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.951  -0.862   1.598  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    9   15
CONECT    3    4    4    8
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8   26
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   31
CONECT   15   16   20   32
CONECT   16   17   33   34
CONECT   17   18   35   36
CONECT   18   19   37
CONECT   19   20   38   39
CONECT   20   40   41
END

HMDB0248759
     RDKit          3D
Azacyclonol
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.6853   -0.1292   -2.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4158   -0.0880   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    1.2406   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    1.8540    1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630    3.1017    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    3.8190    0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    3.2741   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    2.0383   -1.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564   -1.2183   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -2.2900   -0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -3.4122   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -3.4553    0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070   -2.4195    1.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -1.3122    1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -0.4027   -0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    0.6131   -1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231    0.0119   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712    0.3013    0.1334 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009    0.1317    1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -0.7759    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.3619   -2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.3376    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056    3.5557    2.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1184    4.8267    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225    3.8613   -1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.6459   -1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -2.3190   -1.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3374   -4.2375   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029   -4.3450    1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593   -2.4853    2.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -0.5033    1.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.3222   -1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516    1.6073   -0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449    0.5769   -2.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880    0.4067   -1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.0988   -1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -0.0776    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -0.3806    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400    1.0930    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267   -1.8005    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -0.8617    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 20 15  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Azacyclonol hydrochloride	MeSH
Psychosan	ChEMBL
Calmeran	ChEMBL
Ataractan	ChEMBL
Frenquel	ChEMBL
Frenoton	ChEMBL
gamma-Pipradol	ChEMBL
g-Pipradol	Generator
γ-pipradol	Generator
Azacyclonol	MeSH

Chemical Formula

C₁₈H₂₁NO

Average Molecular Weight

267.372

Monoisotopic Molecular Weight

267.1623143

IUPAC Name

diphenyl(piperidin-4-yl)methanol

Traditional Name

azacyclonol

CAS Registry Number

Not Available

SMILES

OC(C1CCNCC1)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H21NO/c20-18(15-7-3-1-4-8-15,16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,17,19-20H,11-14H2

InChI Key

ZMISODWVFHHWNR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aralkylamine
Piperidine
Tertiary alcohol
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Aromatic alcohol
Alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.36	ALOGPS
logP	2.88	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	10.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.22 m³·mol⁻¹	ChemAxon
Polarizability	30.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	163.046	30932474
DeepCCS	[M-H]-	160.688	30932474
DeepCCS	[M-2H]-	193.574	30932474
DeepCCS	[M+Na]+	169.139	30932474
AllCCS	[M+H]+	164.7	32859911
AllCCS	[M+H-H2O]+	161.1	32859911
AllCCS	[M+NH4]+	168.0	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	166.8	32859911
AllCCS	[M+Na-2H]-	166.6	32859911
AllCCS	[M+HCOO]-	166.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azacyclonol	OC(C1CCNCC1)(C1=CC=CC=C1)C1=CC=CC=C1	2597.8	Standard polar	33892256
Azacyclonol	OC(C1CCNCC1)(C1=CC=CC=C1)C1=CC=CC=C1	2219.1	Standard non polar	33892256
Azacyclonol	OC(C1CCNCC1)(C1=CC=CC=C1)C1=CC=CC=C1	2228.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Azacyclonol,2TMS,isomer #1	C[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC1	2381.5	Semi standard non polar	33892256
Azacyclonol,2TMS,isomer #1	C[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC1	2361.7	Standard non polar	33892256
Azacyclonol,2TMS,isomer #1	C[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC1	2909.9	Standard polar	33892256
Azacyclonol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC1	2900.0	Semi standard non polar	33892256
Azacyclonol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC1	2753.5	Standard non polar	33892256
Azacyclonol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC1	3050.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Azacyclonol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-4900000000-685d0996e1bcf6e3c6a1	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacyclonol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacyclonol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacyclonol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacyclonol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacyclonol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 10V, Positive-QTOF	splash10-014i-0090000000-254a7394747d59214935	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 20V, Positive-QTOF	splash10-014i-2190000000-51b009d60985aed2c044	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 40V, Positive-QTOF	splash10-05o3-9110000000-ff6a52a8481077ba6266	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 10V, Negative-QTOF	splash10-014i-0190000000-4f6e6ea8d6f232b7219c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 20V, Negative-QTOF	splash10-017i-9270000000-64a85c5a292ddb24e48d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 40V, Negative-QTOF	splash10-0059-9110000000-ed9ab57f7be366b2755b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 10V, Positive-QTOF	splash10-0uxr-0090000000-ab92cce1c56cfd2c8790	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 20V, Positive-QTOF	splash10-0udi-0090000000-c380283f47f31f0937b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 40V, Positive-QTOF	splash10-001i-9520000000-af663b1d51ba4af24fa9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 10V, Negative-QTOF	splash10-014i-0390000000-4a0bb722f3f05bd9893f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 20V, Negative-QTOF	splash10-000i-1930000000-f32c0b27e86aa9c5e50f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacyclonol 40V, Negative-QTOF	splash10-03di-0090000000-1f4e1c77bccde6d52d61	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azacyclonol

METLIN ID

Not Available

PubChem Compound

15723

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Azacyclonol (HMDB0248759)

MOL for HMDB0248759 (Azacyclonol)

3D MOL for HMDB0248759 (Azacyclonol)

3D SDF for HMDB0248759 (Azacyclonol)

3D-SDF for HMDB0248759 (Azacyclonol)

PDB for HMDB0248759 (Azacyclonol)

3D PDB for HMDB0248759 (Azacyclonol)

SMILES for HMDB0248759 (Azacyclonol)

INCHI for HMDB0248759 (Azacyclonol)

Structure for HMDB0248759 (Azacyclonol)

3D Structure for HMDB0248759 (Azacyclonol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra